


Game Night

by ravenousfangirl



Category: Supernatural
Genre: Bottom Cas, Crossdressing, Dresses, Feminization, Friends to Lovers, Gay Sex, Love Confessions, M/M, Making Out, Panties, Post-Coital Cuddling, Top Dean
Language: English
Status: Completed
Published: 2014-03-13
Updated: 2014-03-13
Packaged: 2018-01-15 13:15:41
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,027
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1306144
Author URL: https://archiveofourown.org/users/ravenousfangirl/pseuds/ravenousfangirl
Summary: <blockquote class="userstuff">
              <p>Cas was late for Game Night again so Dean went to go pick him up but he finds his best friend in a dress, twirling around his room. And fuck was it turning Dean on.</p>
            </blockquote>





	Game Night

**Author's Note:**

> A little something from Omegle and I just touched it up a bit. Enjoy~

Cas held his breath as he pulled up the socks that rested in the middle of his upper thigh, and placed the light blue sundress over his head. It was his deep dark secret, Castiel Novak liked to wear dresses and whatnot and he intended to keep it that way. When no one was around this is what he did. He let out the breath as he looked at himself in front of his bedroom mirror; a graceful smile appeared on his face when he saw how he looked, amazing. He twirled it around a little, liking how the fabric felt on his clean shaved thigh, and how it looked. When he did this he was in his own little world, where no one could intrude, it was just him and his happiness. He was too distracted to hear that someone had entered his house.

Dean looked around his friends house, shaking his head and making a mental note to remind him to lock the doors for once. He was not going to be late for game night with Sam and his girlfriend. He walked up the stairs and gently pushed Cas' door open. "Cas, do you never answer your phone? Sam and Je-" He cut himself off when he saw his best friend in a dress. Thigh highs and a dress. A dress that may or may not have brought out Cas' eyes.

Cas smiled to himself and played with the dress a little, he twisted himself around to check if it fit right and to see what it looked like from the back when suddenly his door was opened. His mouth dropped open as he looked at Dean through the mirror and for a moment or two he was speechless, his mind racing with thoughts and questions "Dean- this isn't what I looks like I swear!" he begged as he turned to see Dean, "all of my other clothes are dirty and too small this is all I had to wear" he stated hurriedly.

Dean gave Cas a soft smile and chuckled, looking at his full closet behind him. God his friend was a horrible liar, but hell the dress made him look even more innocent and it was kinda turning him on. "We uh- we...game night. Sam and Jess." Was all he could mumble out at that second before collecting himself. "Really though, why are you in a dress?" he asked calmly.

Cas panicked when Dean started to chuckle at him, why was he chuckling at him? Was he going to make fun of him or tell the entire school? "Oh game night? With Sam and jess" he said with a distant nod. He played with the hem of the dress as he answered Dean "I well- s-sometimes, I like to wear dresses. They make me feel...happy." he said quietly. "But-but I only wear them when I'm home alone, not in public" he said hurriedly to make a point.

Dean stepped forward and put a hand over Cas' which were playing with the dress. "I won't tell anyone. I promise. I'm sorry I barged in here without knocking and interrupted a private moment." He said before flashing him his famous Winchester smile. "By the way you look pretty cute in that dress." He complimented, rubbing his thumb over the back of Cas' hand. Dean was thinking about manning up and finally telling Cas his feelings for a while but he didn't want to scare his friend away, especially not after he was already embarrassed to be found like this.

A relieved smile graced Cas' face when Dean said he wouldn't tell anyone, his entire body relaxed and he let out a breath that he didn't realize he was holding. "Thanks so much Dean, it's not that I didn't trust you are anything it's just......a guy wearing a dress, not exactly normal" he huffed in a little laugh as he pulled Dean into a quick hug. "Don't worry, you didn't mean any harm by it right?" Cas smiled when Dean told him he looked cute. "You think so? I just got it a few day's ago and I wasn't sure." he said looking down at the dress and swishing it a little.

Dean smiled at his friend and stepped back to sit on the corner of his bed. "It looks nice. Do you uh..have any other dresses?" he asked, trying to sound less creepy and more casual. "The blue looks nice but a nice pink would be cute too." He said, looking Cas up and down to actually see the whole outfit for once. Fuck he looked adorable and Dean wanted to see him in a dress more often now.

Cas nodded "Yea actually I do, would-would you like to see them?" he asked pointing to the closet, "I have a white and pink one just wait out here." he said as he disappeared into the closet. It took his a while because he was dressing in his closet but he managed, he popped out of the closet wearing a neck strap dress. The bottom was plain pink as well as the stripe of felt that went on the high waist. The top where the breasts were supposed to go was pink with whit dots. "What do you think?' he asked twirling around a little.

Dean got up and walked over to Cas, staring down at him and taking a deep breath. The pink did look better on him. "You look..really good..like amazing." He breathed, gently bringing his hands up to rest on Cas' hips. Now or never Winchester. He took another breath and leaned down, capturing Cas' lips with his own.

Cas tilted his head to the side when Dean approached him "Thanks, this one is my favourite I think." Suddenly he felt Dean's hands on his hips "Dean what-?" he asked before Dean leaned down and place his lips on his own. Cas froze for a moment, not really understanding what was happening at the moment. When he finally came to he gently placed one hand on Dean's chest, slightly clutching his shirt and he timidly kissed back with his eyes closed.

Dean smiled into the kiss and slowly pulled away for air. "I've been wanting to do that for a while now." He admitted, tugging Cas closer against his chest. "I also have had a huge crush on you since like freshman year." he said with a small chuckle, hoping Cas wouldn't kick him out of his room. He bent his head down and nuzzled under his jaw, planting little kisses on his neck.

"For a while?" he asked his cheeks pink, he was a tiny bit flustered at the moment due to the fact that his best friend just kissed him. Cas naturally fell into Dean's chest "Seriously? since freshman year? Why didn't you tell me?" he asked as Dean bent his head down. He tilted his head to the side as Dean started to place tiny kisses on his neck.

"Wasn't sure how you'd react." He mumbled between kisses. "Scared you'd never talk to me again." Dean gently nipped at his ear before pulling his head back up, happy to see his marks on Cas. "I didn't want to lose you as a friend but here and now I didn't really care anymore. I'm done running from it Cas, I-I want you." He flushed a bit at the end but ignored it, bringing a hand up to cup Cas' cheek and plant another kiss on his lips. \

Cas bit his lip as he listened to Dean's explanation, a small gasp left him as his ear was gently nipped. He looked up at Dean and blushed when Dean finally admitted his feeling towards him. A warm hand touched his cheeks as Cas realized that he hadn't said anything back yet.Cas gently placed a hand over Dean's as his eyes fluttered close and there lips met again. He kissed back a little more confidently this time, his heart was pounding in his ears.

Dean was feeling like he could do cartwheels and dance around but he stayed relaxed when Cas' kissed back. He had to force himself to back off before he pushed Cas' against a wall and ravished him all night. "So do you want to go join Sam and Jess or you wanna stay here?" He asked. Not really caring where Cas' chose as long as he got to be with him.

Cas was breathless when they broke the kiss, he could hardly focus on anything really. He swallowed as he blinked a few times, Dean's voice bringing him back down to reality. "I- uh what-what do you want to do?" he asked flustered. Dean chuckled at how adorable Cas was right now. "Well I'd much rather stay here and continue to kiss you, if you don't mind doing that." he said, slowly walking backwards to Cas' bed and sitting down, pulling Cas into his lap when he was situated. He gently ran his hands up and down Cas' thighs, gasping when he left the soft shaved skin.

Cas nodded a small shy smile grew on his face "Yea I think I'd like that as well" he admitted quietly as Dean backed up towards his bed and sat down. He sat comfortably in Dean's lap, resting his hands on his shoulders. Dean's hands felt calloused yet somehow soft on his legs, he bit his lip at the gasp "It makes the socks easier to put on." he said shyly. Dean just stared at Cas like he was the best thing in the world because he practically was. "Ya know I might have to start getting you dresses for your birthday." He said, taking Cas' ass in his hands and pulling him flush against his chest. "So beautiful." He muttered, kissing him again.

Cas smiled "I've had my eye on a few you know" he said with a small laugh "I could take you shopping with me." A small gasp left his lips as hands covered his ass and he was right against Dean's chest. He kissed back as his hands ran through Dean's hair, "Dean, I'm uh also wearing-" he said quietly as he glanced down a little. Dean raised an eyebrow and lifted the hem of Cas' dress up, groaning when he saw the lace panties. "Oh that's hot." He whispered, slowly palming Cas through his panties. "Me and you, we'll go get you some dresses and nice stuff tomorrow mkay? Get you more socks and panties, make you all pretty." He breathed, nipping at Cas' jaw.

Cas blushed "If I don't wear them then you can see the underwear line through the outfit from my normal underwear-." He was cut off when Dean started to palm him through his panties, a soft moan leaving his lips. He nodded mindlessly "Y-yeah okay" he breathed as Dean nipped at his jaw. Dean fell onto his back, pulling Cas with him. He moved his hand and rocked his hips up to show his arousal. "You've ever done this before?" He asked breathlessly. "Don't wanna hurt you." He gasped against his skin, sure to leave more marks.

Cas blushed as he felt Dean's erection against his, involuntarily rolling his hips down and his breath hitching at the sensation. "Um not-not with a person, I have used....equipment." he stated shyly. He knew that he was going to have marks that would be hard to hide, but at this point he didn't care, he went for Dean's mouth, pulling him into a heated kiss. Dean rolled them over, smiling when he was over Cas. He reached under Cas' dress and gently pulled the panties off him, dropping them on the floor. He took his own clothes off until he was stark naked. He fished a packet of lube from his jeans and a condom as well. "If I hurt you, you gotta tell me alright?" He asked.

Cas bit his lip when his panties were removed, his member released from the confines of the panties. He watched as Dean's took off his clothes, he always forgot how jacked Dean was. He nodded, his heart racing "I will" he breathed, "D-Dean what about my dress?" Dean ran a hand down the soft material. "You just look so pretty in it, don't even wanna take it off you. But I promise next time I will." He winked, opening the lubricant packet with his teeth and generously coating his fingers. He gave Cas a genuine soft smile before slowly working one finger into him. 

Cas blushed and swallowed as Dean's hand went down the fabric of the dress, his body arching into the warmth of Dean's hand. He bit his lip as Dean's finger slowly entered him, he had done it to himself before but with the situation and the fact that it was someone else, it made everything a little more intense. he willed himself to relax as he lightly gripped the sheets, his member painfully hard already. Dean added another finger, careful to not hurt Cas because he'd never be able to forgive himself if he did. He slid his fingers out and sat up to roll the condom on, slicking himself up before slowly entering Cas and waiting until he got used to the feeling. 

Cas started to pant as Dean added another finger, quickly losing his composure. He watched Dean roll on the condom, his heart racing fast. He might have underestimated Dean's size as he first entered him, rolling his head back as his breath hitched, although it did hurt a little the pain quickly melted into pleasure. Dean started out with gentle shallow thrusts before quickening his thrusts. He bent down, swallowing down all of Cas' little noises with his mouth while sliding a hand under the dress to jerk Cas' member in time with his thrusts. 

Cas gave out little moans and cries of pleasure as Dean started to thrust into him. He alternated between rolling  his hips back to meet with Dean and thrusting into his hand that was stroking his dick. He brought his legs up to wrap around Dean, encouraging him. On a particular thrust Dean his directly onto his prostate, it made Cas cry out and arch his back off of the bed with a loud moan. Dean watched Cas cry out and he made sure to his that same spot again, wanting to hear more noises from Cas. "Fuck, just look at you." He groaned against Cas' skin, unable to hold himself back as he thrust harder into Cas. "So good Cas."

Cas didn't know how much longer he could last like this, Dean hitting that spot over and over again, he couldn't take it. "D-Dean" he moaned "I-I can't I'm gonna-" he panted hard as he felt a warm coil in his stomach begin to build up. Dean nodded with a grunt. "Same here Cas, so close." he murmured, speeding up his thrusts and jerking Cas faster to send him over the edge first. The thought of him dirtying up his dress made him groan as he almost came right then and there. 

Cas came with a loud moan, his back arching up off the bed and stars exploding behind his eyes as they flew shut. His cum splattered on his dress leaving a large wet mark, his entire body went to the consistency of noodles and he could of sworn to god he passed out. He mewled as Dean thrust into him, looking up at him with glazed eyes. Dean came just from the sight of Cas losing it, his hips stuttering. He gently pulled out and took the condom off, tying it and dropping it onto the floor. He collapsed next to Cas and took his hand, leaning over and kissing him. "So gorgeous." He mumbled. Cas' eyes were still closed, breathing hard as he gently came down from his high. He felt Dean fall next to time and smiled into the kiss, he lazily turned his head and open his eyes "That was.....wow" was all he could say, he looked down at his dress seeing the stain "Aw my dress" he said lifting it a little "I don't know if this'll wash out"

Dean chuckled and sat up a bit to look at it. "Sorry about ruining your dress. We'll get you more tomorrow." He promised, pulling Cas to sit up a bit so he could slid the dress off him. He set it down on the floor before pulling Cas into his arm. "You think Sam and Jess will be mad at us?" He asked. Cas rolled his eyes as Dean pulled him up, he gasped a little at the warm to cold transition but soon found heat from Dean's body. "Nah" he said as he setteled against Dean "I think they'll be good on there own." Dean carded his fingers though Cas' hair, face growing serious. "Do you uh..wanna be my boyfriend?" He asked, biting his lip nervously as he looked down at Cas in his arms. A small part of him was nervous he'd say no but after all that, why would he? 

"No Dean especially after we made out and had sex, why on earth would I ever do that?" he stated sarcastically "Yes Dean of course I would. Just one question, since when were you gay?"

"Since I realized I had a crush on you. I just stopped looking at girls and focused on you." He answered with a shrug. "What about yourself?" He asked, staring up at Cas' ceiling fan.

"I just kind of realized it when I found guys more interesting than girls, nothing personal I just like guys more that's all. I didn't really tell anybody though, although I'm pretty sure everyone assumes that already so" he said with a small laugh. Dean kissed Cas' nose. "Well as long as they didn't make fun of you then I don't have to punch anybody's face in." He said, looking over at him. "But if they do, I will not hesitate to break their noses."


End file.
